2,8-Dioxabicyclo[3.3.1]non-6-en-3-one, 9-ethenyl-6-[(beta-D-glucopyranosyloxy)methyl]-, (1R,5S,9R)-

Details

• Internal ID: cb255e1c-c341-41de-b440-90df8eb1a2f3
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: 9-ethenyl-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,8-dioxabicyclo[3.3.1]non-6-en-3-one
• SMILES (Canonical): C=CC1C2CC(=O)OC1OC=C2COC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C=CC1C2CC(=O)OC1OC=C2COC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C16H22O9/c1-2-8-9-3-11(18)25-15(8)22-5-7(9)6-23-16-14(21)13(20)12(19)10(4-17)24-16/h2,5,8-10,12-17,19-21H,1,3-4,6H2
• InChI Key: OGVKNDDWHJWQJZ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₉
• Molecular Weight: 358.34 g/mol
• Exact Mass: 358.12638228 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.59
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 104777-65-3
• 2,8-Dioxabicyclo[3.3.1]non-6-en-3-one, 9-ethenyl-6-[(beta-D-glucopyranosyloxy)methyl]-, (1R,5S,9R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6277	62.77%
Caco-2	-	0.8825	88.25%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6902	69.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8362	83.62%
OATP1B3 inhibitior	+	0.9541	95.41%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8349	83.49%
P-glycoprotein inhibitior	-	0.8627	86.27%
P-glycoprotein substrate	-	0.8616	86.16%
CYP3A4 substrate	+	0.5698	56.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8739	87.39%
CYP3A4 inhibition	-	0.9044	90.44%
CYP2C9 inhibition	-	0.9255	92.55%
CYP2C19 inhibition	-	0.8235	82.35%
CYP2D6 inhibition	-	0.9068	90.68%
CYP1A2 inhibition	-	0.8981	89.81%
CYP2C8 inhibition	-	0.6504	65.04%
CYP inhibitory promiscuity	-	0.8374	83.74%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7114	71.14%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.9393	93.93%
Skin irritation	-	0.7994	79.94%
Skin corrosion	-	0.9459	94.59%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4575	45.75%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	-	0.6093	60.93%
skin sensitisation	-	0.8430	84.30%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.6290	62.90%
Acute Oral Toxicity (c)	III	0.3794	37.94%
Estrogen receptor binding	-	0.4847	48.47%
Androgen receptor binding	+	0.5387	53.87%
Thyroid receptor binding	-	0.5064	50.64%
Glucocorticoid receptor binding	-	0.5624	56.24%
Aromatase binding	-	0.5520	55.20%
PPAR gamma	+	0.5876	58.76%
Honey bee toxicity	-	0.7645	76.45%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8306	83.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.52%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.16%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.66%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.28%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.84%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.68%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.28%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.21%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	83.15%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.20%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.60%	95.89%
CHEMBL4040	P28482	MAP kinase ERK2	80.65%	83.82%

Plants that contains it

• Sambucus ebulus

Cross-Links

• PubChem: 73798769
• LOTUS: LTS0245124
• wikiData: Q105191889